Downtown Annapolis and the holidays have a deep and nearly timeless relationship. It is where families have traditionally congregated to celebrate, eat and shop. This year will be no different as the Downtown Annapolis Partnership hosts Annapolis’ favorite shopping nights for locals, Midnight Madness. This year, Midnight Madness will be held on December 3 and December 10 until midnight and on December 17 until 11:00pm.
Downtown Annapolis — including West Street, Maryland Avenue, Main Street and the City Dock area — will be filled with traditional holiday decorations including beautiful storefront windows, garland, wreaths, holiday lights, a snowflake alley, light canopies, a large Christmas tree and a menorah.
“You will love strolling outdoors, shopping and dining in the historic district of Annapolis this holiday season,” said Erik Evans, the executive director of the Downtown Annapolis Partnership.
Annapolis has been named as one of the best Christmas towns to visit for the holidays by Country Living and one of the most festive Christmas cities in the USA by 24/7 Wall Street. This is in strong part due to events like the Light Parade and Midnight Madness.
Critical to the success of this year’s holiday events is keeping everyone safe. So, in addition to the standard COVID-19 safety protocols of requiring a mask while shopping, limiting the number of people in a store, encouraging frequent handwashing and telling people if they are sick to stay home, other safety protocols will be added to the list. Both Main Street and Maryland Avenue will be closed to cars during Midnight Madness nights to allow more space for pedestrians to socially distance. This space will also be used for tents for outdoor dining, some outdoor retail space, as a place to queue customers waiting to get inside a store, and to move some small-scale entertainment away from the sidewalks.
The event shopping hours will also start two hours earlier this year at 4:00pm. This provides another opportunity for people to spread out arrival times and reduce crowding. By shopping during either the first two hours or the final two hours of Midnight Madness, shoppers can avoid the typical primetime hours. The city has extended the hours restaurants can operate outdoors and in heated tents to give hungry shoppers more time to support local businesses. For those unable to enjoy these shopping events in person, the Downtown Annapolis Partnership has made it easy to shop with downtown Annapolis businesses online at www.midnightmadnessannapolis.com.
In addition to the late-night shopping on Thursdays during Midnight Madness, many of the stores in downtown Annapolis will add later shopping hours (until 9:00pm) in December, especially on Friday and Saturday evenings. Look for the new “Open Late for Safe Shopping” flags that merchants can put up on evenings they are open late.
Additional outdoor holiday events scheduled include Small Business Saturday in downtown Annapolis on November 28, Artist Sunday throughout Annapolis on November 29, the First Sunday Arts Holiday Market on West Street on December 6, and the Eastport Yacht Club Light Parade along Spa Creek on December 12.
Free garage parking for the holidays will be more plentiful than ever in downtown Annapolis with four parking garages offering long-term, free holiday parking.
Free parking garage options include:
For short-term parking, the parking meters will be free for the first two hours for everyone. A bonus free hour at the meters is available by using the code ParkDTA on the Parkmobile App.
For additional information on Midnight Madness and other downtown Annapolis holiday events, visit the Downtown Annapolis Partnership’s website at www.downtownannapolispartnership.org.